Shopping & More in Downtown Woodstock, VT

Jackson House Inn, Woodstock Vermont

There are four seasons worth of reasons to escape for a bit of luxury and pampering at our Woodstock, VT Bed and Breakfast. From fall beauty and a charming winter wonderland to beautiful trails and recreation in spring and summer, there is always plenty worth doing, including shopping in downtown Woodstock, VT.

Discovering the charms of downtown Woodstock, VT is perhaps best enjoyed after the busy summer and fall crowds have gone home and before the seasonal festivities of a Woodstock, Vermont Christmas. If a relaxed, slow-paced getaway with delicious breakfasts, elegant accommodations, and exceptional hospitality sounds like something you’re interested in this autumn, it’s time to book a room at the Jackson House Inn. 

The Jackson House Inn is the leading Woodstock, VT Bed and Breakfast. We offer guests refined luxury in a timeless and modern setting. In short, it’s precisely the kind of getaway even the most discerning guests are looking for. We’re located close enough to downtown Woodstock, VT for you to enjoy the shops, restaurants, and more, but far enough away to feel as though you’ve truly had some time and space to yourself. Head to our website and reserve your spot at our Woodstock, VT Bed and Breakfast today!

Woodstock VT Hotel & Bed and Breakfast Lodging Options from Jackson House Inn
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The exterior of the bookstore in downtown woodstock, VT

Enjoy the Best of Downtown Woodstock, VT

Aside from emanating a never-ending sense of charm and in the best kind of throwback to a different time and place, there are excellent opportunities for shopping in downtown Woodstock, VT. In fact, it’s a fantastic place to check a few items off your holiday shopping lists as we head into the festive season!

You’ll find an incredible array of shops in downtown Woodstock, VT. The streets are lined with historic buildings filled with independently owned boutiques and artisan goods. You’ll find bookshops, art galleries, toy stores, general stores, restaurants, and so much more.

Shopping the streets of downtown Woodstock, VT is one of our favorite things to do in town and is a wonderful way to spend at least one afternoon while you’re visiting the Jackson House Inn. Below, you’ll find a list of a few of our favorite ways to spend a day in downtown Woodstock, VT. 

  1. No visit to downtown Woodstock, VT is complete without a visit to F.H. Gillingham & Sons. It’s a fantastic general store that offers a wonderful assortment of all things Vermont.  
  2. Another “must” for avid shopping in downtown Woodstock, VT is the Yankee Bookshop, which has been in business since 1935 and is the state’s longest-running independent bookstore. Their curated collection of books and gifts is top-notch!  
  3. When you’re ready for lunch, you can’t go wrong with a meal at Mon Vert Cafe, known for using organic, locally sourced ingredients. 
  4. After lunch, take a short walk across the Middle Covered Bridge and enjoy some scenery in downtown Woodstock, VT, before continuing your shopping adventure.
  5. Head to Farmhouse Pottery or Collective, The Art of Craft for fantastic artisan-made gifts. 
  6. Another fantastic gift shop to peruse is Clover Gift Shop, known for its unique, curated collection of gifts and home goods.
  7. If you’re shopping for a little one in downtown Woodstock, VT, you won’t want to miss the charming, toy-laden world of Red Wagon Toy Co.  
  8. If you have an art lover in your life or you’re looking to add something unique to your walls, you won’t want to miss a stop at Focus Gallery in downtown Woodstock, VT. 

There are also some wonderful opportunities for antiquing in downtown Woodstock, VT. Who knows what untold treasures await? 

Woodstock VT Hotel & Bed and Breakfast Lodging Options from Jackson House Inn
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View of the exterior of our Woodstock Vermont Bed and Breakfast, located near downtown Woodstock, VT

The Best Woodstock Vermont Bed and Breakfast

Though there are plenty of ways to keep busy in Woodstock this fall, including charming adventures into downtown Woodstock, VT, there’s only one true way to relax: indulging in a getaway at our Woodstock, VT Bed and Breakfast. We offer a one-of-a-kind lodging experience that is beyond compare, often far exceeding the expectations of even our most discerning guests. 

Staying at our Woodstock, VT Bed and Breakfast is an all-encompassing experience. Despite the town’s charms and the natural beauty on Woodstock’s surrounding trails, there’s little reason to leave the quiet, upscale comforts of the Jackson House Inn. As you wake up in the morning, we’ll treat you to a delicious, house-made breakfast focused on seasonal and local ingredients. It’s served in our breathtaking dining room that overlooks our well-landscaped grounds and is furnished with custom pieces from our friends at Shakelton Thomas

Our Woodstock, VT Bed and Breakfast offers eleven distinct guest rooms, each designed with our guests’ comfort at the top of mind. The spaces are elegant, well-decorated, and outfitted with various high-end amenities to complement your getaway. There are plenty of areas inside and out to relax, unwind, and enjoy a delicious house-made cocktail or a selection from our extensive wine and beer collection. 

Getaways at our Woodstock, VT Bed and Breakfast are exactly what they should be – beautiful, indulgent, and relaxing. We’d love to share a little space with you this fall or winter. Book a room at our Woodstock, VT Bed and Breakfast today!

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